PL196774B1 - Pochodne indolilopiperydyny jako środki przeciwhistaminowe i przeciwalergiczne - Google Patents

Info

Publication number

PL196774B1

PL196774B1 PL353164A PL35316400A PL196774B1 PL 196774 B1 PL196774 B1 PL 196774B1 PL 353164 A PL353164 A PL 353164A PL 35316400 A PL35316400 A PL 35316400A PL 196774 B1 PL196774 B1 PL 196774B1

Authority

PL

Poland

Prior art keywords

ethoxy

piperidin

indol

ethyl

benzoic acid

Prior art date

1999-06-04

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• HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 title claims abstract description 18
• 239000000739 antihistaminic agent Substances 0.000 title abstract description 9
• 239000000043 antiallergic agent Substances 0.000 title description 5
• 230000001387 anti-histamine Effects 0.000 title 1
• -1 alkylenethio Chemical group 0.000 claims abstract description 168
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
• 125000005843 halogen group Chemical group 0.000 claims abstract description 13
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 9
• 125000005529 alkyleneoxy group Chemical group 0.000 claims abstract description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
• 239000001257 hydrogen Substances 0.000 claims abstract description 8
• 125000001589 carboacyl group Chemical group 0.000 claims abstract description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 4
• 238000000034 method Methods 0.000 claims description 99
• 150000001875 compounds Chemical class 0.000 claims description 97
• 239000000203 mixture Substances 0.000 claims description 82
• 239000002253 acid Substances 0.000 claims description 61
• 239000005711 Benzoic acid Substances 0.000 claims description 56
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 20
• 235000010233 benzoic acid Nutrition 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• QCFSNBWEJWOEPW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-piperidin-4-ylindole Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCNCC1 QCFSNBWEJWOEPW-UHFFFAOYSA-N 0.000 claims description 8
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• GCCYBNZBCGRHRR-UHFFFAOYSA-N methyl 2-(2-chloroethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCCl GCCYBNZBCGRHRR-UHFFFAOYSA-N 0.000 claims description 8
• QSOACFIAXDGTQW-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O QSOACFIAXDGTQW-UHFFFAOYSA-N 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• MIPYJZXZGANVJL-UHFFFAOYSA-N 2-[2-[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(F)=CC=3)C=2)CC1 MIPYJZXZGANVJL-UHFFFAOYSA-N 0.000 claims description 6
• 208000024780 Urticaria Diseases 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 206010010741 Conjunctivitis Diseases 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 5
• AAEZWNBJUPWTNT-UHFFFAOYSA-N tert-butyl 4-(2-chloroethoxy)benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(OCCCl)C=C1 AAEZWNBJUPWTNT-UHFFFAOYSA-N 0.000 claims description 5
• WBMYDORIDCSVSO-UHFFFAOYSA-N 2-[2-[4-(1-pentylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O WBMYDORIDCSVSO-UHFFFAOYSA-N 0.000 claims description 4
• NDRPQPJPFUMFQZ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O NDRPQPJPFUMFQZ-UHFFFAOYSA-N 0.000 claims description 4
• AARSYHRXVGSQHM-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O AARSYHRXVGSQHM-UHFFFAOYSA-N 0.000 claims description 4
• HIKYNJRMLYWZMO-UHFFFAOYSA-N 2-[3-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC1=CC=CC=C1C(O)=O HIKYNJRMLYWZMO-UHFFFAOYSA-N 0.000 claims description 4
• OLYGEFPXSWBWOU-UHFFFAOYSA-N 3-[3-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC1=CC=CC(C(O)=O)=C1 OLYGEFPXSWBWOU-UHFFFAOYSA-N 0.000 claims description 4
• PKJMGCNGLZTAFR-UHFFFAOYSA-N 3-[3-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CCCOC1=CC=CC(C(O)=O)=C1 PKJMGCNGLZTAFR-UHFFFAOYSA-N 0.000 claims description 4
• XGQCLGOTLVBAIE-UHFFFAOYSA-N 3-[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCC1C(C1=CC=CC=C11)=CN1CC1=CC=C(F)C=C1 XGQCLGOTLVBAIE-UHFFFAOYSA-N 0.000 claims description 4
• ZSGZESFWXBUNED-UHFFFAOYSA-N 3-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]propanoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C1CCN(CCC(O)=O)CC1 ZSGZESFWXBUNED-UHFFFAOYSA-N 0.000 claims description 4
• GZMZUFPMBUYDFX-UHFFFAOYSA-N 4-[3-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CCCOC1=CC=C(C(O)=O)C=C1 GZMZUFPMBUYDFX-UHFFFAOYSA-N 0.000 claims description 4
• JPHSHTODQABXIL-UHFFFAOYSA-N 5-[[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidin-1-yl]methyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(F)=CC=3)C=2)CC1 JPHSHTODQABXIL-UHFFFAOYSA-N 0.000 claims description 4
• KYQXAYYQCREFNM-UHFFFAOYSA-N 5-[[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]methyl]furan-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CC1=CC=C(C(O)=O)O1 KYQXAYYQCREFNM-UHFFFAOYSA-N 0.000 claims description 4
• 206010048768 Dermatosis Diseases 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 206010039083 rhinitis Diseases 0.000 claims description 4
• 208000017520 skin disease Diseases 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• DUCZGLRXKNHEME-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-[1-[3-[4-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC(C=C1)=CC=C1C=1N=NNN=1 DUCZGLRXKNHEME-UHFFFAOYSA-N 0.000 claims description 3
• ISRNSOPKRJFRMR-UHFFFAOYSA-N 1-(3-methylbutyl)-3-[1-[3-[2-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCCOC1=CC=CC=C1C=1N=NNN=1 ISRNSOPKRJFRMR-UHFFFAOYSA-N 0.000 claims description 3
• ZDRUIODKMKJGOJ-UHFFFAOYSA-N 1-(3-methylbutyl)-3-[1-[3-[4-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCCOC(C=C1)=CC=C1C=1N=NNN=1 ZDRUIODKMKJGOJ-UHFFFAOYSA-N 0.000 claims description 3
• VMEWUJUJGKNDJZ-UHFFFAOYSA-N 2-[2-[4-(1-hexylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O VMEWUJUJGKNDJZ-UHFFFAOYSA-N 0.000 claims description 3
• KTEZZEXASTZNJG-UHFFFAOYSA-N 2-[2-[4-(1-prop-2-enylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=C)C=2)CC1 KTEZZEXASTZNJG-UHFFFAOYSA-N 0.000 claims description 3
• QLHLGBNHXMZIQT-UHFFFAOYSA-N 2-[2-[4-(1h-indol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3NC=2)CC1 QLHLGBNHXMZIQT-UHFFFAOYSA-N 0.000 claims description 3
• HHITYXUJELSBPS-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-4-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O HHITYXUJELSBPS-UHFFFAOYSA-N 0.000 claims description 3
• SPOKTOSVUQLTOH-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-4-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O SPOKTOSVUQLTOH-UHFFFAOYSA-N 0.000 claims description 3
• QMFNTTFIGWXQNY-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O QMFNTTFIGWXQNY-UHFFFAOYSA-N 0.000 claims description 3
• INVVRCPLVVQOGS-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O INVVRCPLVVQOGS-UHFFFAOYSA-N 0.000 claims description 3
• DGVYELQBTIBCMU-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O DGVYELQBTIBCMU-UHFFFAOYSA-N 0.000 claims description 3
• HOLMXWXLIIOTTC-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O HOLMXWXLIIOTTC-UHFFFAOYSA-N 0.000 claims description 3
• WYMKMMPHJBIHRY-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O WYMKMMPHJBIHRY-UHFFFAOYSA-N 0.000 claims description 3
• KGKISXJBNCHPAU-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O KGKISXJBNCHPAU-UHFFFAOYSA-N 0.000 claims description 3
• XUQURAFGTLVXHN-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O XUQURAFGTLVXHN-UHFFFAOYSA-N 0.000 claims description 3
• BVRIYQUZSCWOSG-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O BVRIYQUZSCWOSG-UHFFFAOYSA-N 0.000 claims description 3
• WUAPZVZDCHYLGI-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-7-methylindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=CC(C)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O WUAPZVZDCHYLGI-UHFFFAOYSA-N 0.000 claims description 3
• XUYOZHRTHKAKTL-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O XUYOZHRTHKAKTL-UHFFFAOYSA-N 0.000 claims description 3
• OBUAFUJPNYUMEW-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethylsulfanyl]acetic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCN(CCSCC(O)=O)CC1 OBUAFUJPNYUMEW-UHFFFAOYSA-N 0.000 claims description 3
• LVAJRQDSXRFOTR-UHFFFAOYSA-N 2-[2-[4-[1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O LVAJRQDSXRFOTR-UHFFFAOYSA-N 0.000 claims description 3
• OSFBNDLQBDNFRN-UHFFFAOYSA-N 2-[2-[4-[1-(2-methylpropyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CC(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O OSFBNDLQBDNFRN-UHFFFAOYSA-N 0.000 claims description 3
• NYQGYEGBQNANJM-UHFFFAOYSA-N 2-[2-[4-[1-(3-methylbutyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O NYQGYEGBQNANJM-UHFFFAOYSA-N 0.000 claims description 3
• VBXUDFDAMGGOQA-UHFFFAOYSA-N 2-[2-[4-[1-(cyclopropylmethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC3CC3)C=2)CC1 VBXUDFDAMGGOQA-UHFFFAOYSA-N 0.000 claims description 3
• VJYYJODZGYTFFM-UHFFFAOYSA-N 2-[2-[4-[1-[(4-methoxyphenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=CC=C2C(C2CCN(CCOC=3C(=CC=CC=3)C(O)=O)CC2)=C1 VJYYJODZGYTFFM-UHFFFAOYSA-N 0.000 claims description 3
• NMUSDIXZEJLCTH-UHFFFAOYSA-N 2-[2-[4-[1-[(4-phenylmethoxyphenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(OCC=4C=CC=CC=4)=CC=3)C=2)CC1 NMUSDIXZEJLCTH-UHFFFAOYSA-N 0.000 claims description 3
• DTTZVMYXKPDNIC-UHFFFAOYSA-N 2-[2-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O DTTZVMYXKPDNIC-UHFFFAOYSA-N 0.000 claims description 3
• DTEVHRPFQBKFKZ-UHFFFAOYSA-N 2-[2-[4-[1-[2-(4-methoxyphenyl)ethyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C1=CC(OC)=CC=C1CCN1C2=CC=CC=C2C(C2CCN(CCOC=3C(=CC=CC=3)C(O)=O)CC2)=C1 DTEVHRPFQBKFKZ-UHFFFAOYSA-N 0.000 claims description 3
• PLUCWLKTQPYMOJ-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O PLUCWLKTQPYMOJ-UHFFFAOYSA-N 0.000 claims description 3
• MWHMBIYNCCYPQI-UHFFFAOYSA-N 2-[2-[4-[5-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O MWHMBIYNCCYPQI-UHFFFAOYSA-N 0.000 claims description 3
• GOWPJVSOMIHDDM-UHFFFAOYSA-N 2-[2-[4-[5-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O GOWPJVSOMIHDDM-UHFFFAOYSA-N 0.000 claims description 3
• LYQYDLDTHBVSBI-UHFFFAOYSA-N 2-[2-[4-[5-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O LYQYDLDTHBVSBI-UHFFFAOYSA-N 0.000 claims description 3
• BLKUTSXBXNFUNN-UHFFFAOYSA-N 2-[2-[4-[5-chloro-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O BLKUTSXBXNFUNN-UHFFFAOYSA-N 0.000 claims description 3
• VUUZVHPYUMSGRB-UHFFFAOYSA-N 2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O VUUZVHPYUMSGRB-UHFFFAOYSA-N 0.000 claims description 3
• XLIGNZHKWRUBOD-UHFFFAOYSA-N 2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O XLIGNZHKWRUBOD-UHFFFAOYSA-N 0.000 claims description 3
• OMSYYPWHMFLIDI-UHFFFAOYSA-N 2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O OMSYYPWHMFLIDI-UHFFFAOYSA-N 0.000 claims description 3
• QWQRGXJHFQEOOM-UHFFFAOYSA-N 2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O QWQRGXJHFQEOOM-UHFFFAOYSA-N 0.000 claims description 3
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• 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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• 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
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